2,3,4-Tri-O-acetyl-1,6-anhydro-β-D-mannopyranose, an artifact produced during carbohydrate analysis. A total synthesis of 2,3,5-tri-O-acetyl-1,6-anhydro-β-D-mannofuranose

Article abstract of DOI:10.1016/0008-6215(93)84078-K

This study confirms that 2,3,4-tri-O-acetyl-1,6-anhydro-β-D-mannopyranose is an artifact produced during carbohydrate analysis. A new synthesis of 2,3,5-tri-O-acetyl-1,6-anhydro-β-D-mannofuranose is also described, and a novel dimer, 1,6':6,1'-dianhydro-2,3:2',3'-di-O-isopropylidene-5,5'-di-O-(1-methoxy ethyl)-di-α-D-mannofuranose, has been isolated. The structure of the dimer is confirmed by X-ray analysis of a derivative, 1,6':6,1'-dianhydro-2,3:2',3'-di-O-isopropylidene-di-α-D-mannofuranos e. This study confirms that 2,3,4-tri-O-acetyl-1,6-anhydro-β-D-mannopyranose is an artifact produced during carbohydrate analysis. A new synthesis of 2,3,5-tri-O-acetyl-1,6-anhydro-β-D-mannofuranose is also described, and a novel dimer, 1,6′:6,1′- dianhydro-2,3:2′,3′-di-O- isopropylidene-5,5′-di-O-(1-methoxyethyl)-di-α-D- mannofuranose, has been isolated. The structural of the dimer is confirmed by X-ray analysis of a derivative, 1,6′:6, 1′-dianhydro-2,3:2′,3′-di-O-isopropylidene- di-α-D-mannofuranose.